Sodium Methoxide → HCID 54249503, compound

HRID 1416967Notes

Reaction equation

HRID 1416967 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[C:4]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[N:3]=1.[CH3:28][O-:29].[Na+]>CO>[CH3:28][O:29][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[C:4]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 54117122HCID 54117122, compound

Product 1

HCID 54249503HCID 54249503, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloro-6-(4-methoxyphenyl)-5-[4-(methylsulfonyl)phenyl]pyridine-3-carbonitrile (Example 8) (100 mg, 0.25 mMol) was added to freshly prepared sodium methoxide (0.27 mMol) in methanol and stirred at room temperature for 22 hours and then at 75° C. for 4 hours. The reaction solution was concentrated and the product was purified by silica gel chromatography to give a white solid. Anal. Calc'd. for C21H18N2O4S (394.45): C, 63.95; H, 4.60; N, 7.10. Found: C, 63.80; H, 4.71; N, 6.94.

Workup

  1. waitat 75° C. for 4 hours
  2. concentrationThe reaction solution was concentrated
  3. customthe product was purified by silica gel chromatography
  4. customto give a white solid

Sources & evidence

ORD record
ord-bc53654467da46bfb381a10a0f262c35
Source dataset
uspto-grants-1999_06
Patent number
US05916905

Reaction notes

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